Sleeps up to 16
Ideal for large families, reunions & groups.
Discover the perfect getaway with our spacious vacation rentals on Hilton Head Island, accommodating up to 16 guests. Ideal for large families, reunions, or group vacations, these properties offer ample space, luxurious amenities, and stunning locations. Enjoy fully-equipped kitchens, multiple living areas, numerous bedrooms, and private pools. Pair these amenities with our signature Luxury Concierge services, and you can rest assured that your vacation will be relaxing and memorable.
Situated close to the island's beautiful beaches, golf courses, tennis & pickleball courts and outdoor activities, our rentals ensure a memorable stay for everyone. Book your Hilton Head Island vacation rental today and experience unparalleled comfort and convenience for your entire group in this picturesque coastal paradise!
21 properties available
Welcome to 5 Jessamine Place, only a 10-minute walk to the best beach on Hilton Head Island!
This ranch-style cottage home is newly renovated and beautifully furnished. It offers four bedrooms and four bathrooms to comfortably host up to 13 guests. Nestled on a quiet street with a big yard and private heated pool plus spa, this home is perfect fo
5 Jessamine Place
House -
$287.00 - $1,131.00 / per night
4
bedrooms
4
baths
13
guests
5
(16)
Nestled within the picturesque surroundings of Palmetto Dunes on Hilton Head Island, South Carolina, this exquisite 5-bedroom house offers the epitome of coastal luxury living. Just a leisurely stroll away from the pristine sandy shores of the beach, this home combines elegant design with breathtaking natural beauty.
Upon entering, you are welcome
189 Mooring Buoy
House -
$319.00 - $1,086.00 / per night
5
bedrooms
4
baths
1
half bath
13
guests
5
(2)
4 Junket sits 2nd row in Palmetto Dunes with Gorgeous Updates, Private Pool, Screened porch and Lowcountry luxury living
This second-row oceanfront, pet-friendly home is the epitome of Lowcountry luxury living on the beach. You are invited to this gorgeous masterpiece with 4 bedrooms, 2 living and dining areas, and a screened porch that sits steps
4 Junket
House -
$414.00 - $1,717.00 / per night
4
bedrooms
4
baths
13
guests
4.8
(20)
This completely remodeled Sea Pines home sits on the 11th fairway and 15th green of the Harbour Town Golf Course!
With 5 bedrooms and 6 bathrooms, this sunlight-filled home can host up to 14 guests comfortably. As you enter the home, you are met with an extremely open floor plan that is designed with sophistication and tastefully decorated. The li
100 Baynard Cove
House -
$511.00 - $1,430.00 / per night
5
bedrooms
5
baths
1
half bath
14
guests
5
(7)
Elegance is understated in this Lowcountry home, truly one of a kind. The setting could not get more perfect. This fabulous home offers 4 bedrooms, 2 master suites, 2 queen bedrooms, and a bunk room. The home boasts multiple living areas on the inside, a gourmet kitchen, and a massive backyard that includes a private pool, covered outdoor living ro
51 Haul Away
House -
$442.00 - $1,306.00 / per night
4
bedrooms
5
baths
14
guests
5
(10)
Welcome to 2 Royal Tern! This charming Sea Pines home is 4th row from the beach and features 5 bedrooms along with 5 bathrooms and 2 half bathrooms to host 14 guests very comfortably.
The first floor features a very open floor plan that offers easy access between the multiple living spaces, kitchen and wet bar, and dining room. Guests can enjoy pl
2 Royal Tern
House -
$533.00 - $2,174.00 / per night
5
bedrooms
6
baths
2
half baths
14
guests
4.9
(12)
Brand New Construction 3rd row home in Palmetto Dunes!
130 Mooring Buoy is a beautiful 5-bedroom, 4.5-bath luxury home nestled in the beautiful Palmetto Dunes Oceanfront Resort. Just three rows from the beach, this home is meticulously designed for your perfect vacation.
With an open first-floor layout, the entire family can spread out without mi
130 Mooring Buoy
House -
$581.00 - $2,276.00 / per night
5
bedrooms
4
baths
1
half bath
14
guests
5
(9)
Welcome to 30 Ruddy Turnstone! With beautiful craftsmanship throughout the well-appointed house. The ground level has a newly refinished pine floor and an open-plan design, with the large kitchen overlooking the cozy living room. There are lots of books to read; there is lots of seating on the sofas; a kitchen bar that seats 4 overlooks the kitchen
30 Ruddy Turnstone | Ruddy Retreat
House -
$438.00 - $1,828.00 / per night
5
bedrooms
6
baths
14
guests
4.9
(11)
This expansive property features five bedrooms and two separate entrances, providing ample space and privacy for larger groups. This property boasts multiple living areas, ensuring plenty of room for everyone to spread out and relax.
This amazing villa features two fully equipped kitchens with modern appliances, ample counter space, and all the ne
1013 Seacrest
Villa -
$456.00 - $1,799.00 / per night
5
bedrooms
5
baths
1
half bath
14
guests
5
(7)
**THIS OCEANFRONT HOME IS A NON-SMOKING PROPERTY (INCLUDING OUTDOOR SPACES) AND DOES NOT ALLOW ANY PETS OR ANIMALS IN OR ON PROPERTY.**
Welcome to the 19th Armada! This stunning oceanfront oasis sits in the heart of Palmetto Dunes. As soon as you step through the front doors, the luxurious coastal vibe greets you with panoramic ocean views. Multi
19 Armada
House -
$1,861.00 - $5,722.00 / per night
6
bedrooms
6
baths
2
half baths
15
guests
5
(9)
Welcome to 9 Flamingo Street in the charming town of Hilton Head! This stunning rental home offers a picturesque and convenient location, perfect for creating unforgettable vacation memories. This two-story retreat is designed for groups, with a private pool, a huge outdoor dining table, and five bedrooms with multiple bunk options. Spread out betw
9 Flamingo Street
House -
$282.00 - $1,322.00 / per night
5
bedrooms
3
baths
1
half bath
15
guests
4.6
(3)
Can you just imagine hearing the birds chirping and the wildlife rustling in the greenery as you watch the herons wading in the lagoon? Can you hear the ping of the golfer’s tee shot? Is the contact between the driver and the golf ball making the sweetest sound? Can you imagine relaxing by the inviting pool while hearing the sizzle of your steak co
42 Stoney Creek
House -
$557.00 - $2,350.00 / per night
7
bedrooms
7
baths
1
half bath
15
guests
4.8
(7)
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